Diisopropylethylamine → HCID 60131304, compound

HRID 132147Notes

Reaction equation

HRID 132147 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C@@H:12]([NH2:14])[CH3:13])=[CH:6][CH:5]=1.[CH2:17]([O:24][C:25]([NH:27][C@@H:28]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C:29](O)=[O:30])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:17]([O:24][C:25](=[O:26])[NH:27][C@H:28]([C:29](=[O:30])[NH:14][C@@H:12]([CH3:13])[CH2:11][NH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:15])([F:16])[F:1])=[CH:9][CH:8]=1)[CH2:32][CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14158015(S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acidHCID 59733160HCID 59733160, compound

Product 1

HCID 60131304HCID 60131304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)—N-(4-trifluoromethoxy-phenyl)-propane-1,2-diamine (76.7 mg, 0.328 mmol), (S)-2-benzyloxycarbonylamino-3-cyclohexyl-propionic acid (100 mg, 0.328 mmol) and HATU (125 mg, 0.328 mmol) were added to a round bottom flask with 20 mL of dry DCM. DIPEA (127 mg, 0.982 mmol) was added dropwise over three minutes with vigorous stirring. The resulting slurry was stirred for 1.5 hours. The solution was then washed with sodium bicarbonate, the organic layer was separated and partially concentrated and the concentrate was purified by flash chromatography. Yield 138 mg, 81%.

Workup

  1. washThe solution was then washed with sodium bicarbonate
  2. customthe organic layer was separated
  3. concentrationpartially concentrated
  4. customthe concentrate was purified by flash chromatography

Sources & evidence

ORD record
ord-4ebee6704a384ae2b1c35f9d64880a11
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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